CN1106792A - Method for decolorization of alkanolamines and alkyleneamines - Google Patents
Method for decolorization of alkanolamines and alkyleneamines Download PDFInfo
- Publication number
- CN1106792A CN1106792A CN94109198A CN94109198A CN1106792A CN 1106792 A CN1106792 A CN 1106792A CN 94109198 A CN94109198 A CN 94109198A CN 94109198 A CN94109198 A CN 94109198A CN 1106792 A CN1106792 A CN 1106792A
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- CN
- China
- Prior art keywords
- alkanolamine
- color
- alkylene amines
- solid
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Color-containing alkanolamines or alkyleneamines, having color numbers of up to 100 PtCo or higher, can be treated with polymeric solid acidic catalysts at elevated temperatures. Perfluorinated ionexchange polymers in the acid form may be used as the polymeric solid acidic catalyst. In the presence of added water, these polymeric solid acidic catalysts produce decolorized alkanolamines or alkyleneamines having color numbers of 20 PtCo or less. The process of decolorization can be carried out in batch or continuous mode processes thus providing low cost, high quality and high purity end products.
Description
The invention relates to the decoloring method of alkanolamine and alkylene amines, especially about the method for batch and continuous production alkanolamine and alkylene amines, this product has the feature of improving color by handling with the polymerization solid acid catalyst.
For the potential user, price and purity are key characters in chemical market.During utilizing commercial run to produce various chemical, impurity usually enters into technological process, and color stain is the most obvious.The root of this color stain may be from the metal and the metallic compound of catalyst system therefor in the technological process or equipment, perhaps from formed conjugation organic compound in the technological process.Change to another procedure from a procedure owing to form the mechanism of these dye discoloration things, so decoloration process normally carries out according to the mechanism in painted source.
As everyone knows, at the preparation alkylene amines, during especially senior polyamines, make it become decolouring, usually can reduce their commercial value.In order to decolour or to improve the color of these compounds, commercially used or proposed many processing methodes, these methods for example comprise, and are disclosed among the UK1351050 as JA-119902, handle with hydrogenchloride or amine salt acidulants; As at high temperature disclosed in US3723529 and 4737243, handle with gac, acid-treated clay or acid zeolite; Handle as the pulverous sulfonic acid ion exchange resin of disclosed usefulness among the US4731165.Each method in these methods all is to be final step with the distillation, to obtain desired color.And, also need other processing step, as in and residue, the processing and the disposal of acid.In certain methods, also need other to make the step of process complications, as the recovery and/or the reactivate of catalyzer.
US4570019 discloses a kind of method, can produce continuously and have the polyalkylenepolyamines that improves color characteristic, this method is included in high temperature to be had under the existence of water, handle the polyethylene polyamine of decolouring with the polyethylene polyamine hydrochloride, therefore, cancelled additional process steps described in the above-mentioned processing method.
Yet as well known in the prior art, the method for the senior ethylidene polyamines that is used to decolour can not be changed as alkanolamine for this compounds; This compounds is to prepare with the different processing methodes reagent different with use.
For example, react with alkylene oxide and ammonia or amine usually and prepare alkanolamine, especially the alkanolamine as the N-aminoethyl ethanolamine generally can be prepared by the reductive amination of monoethanolamine.
By the alkanolamine that these conventional processing methodes make, color can be changed over light yellow by almost colourless water-white liquid.Alkanolamine, especially thanomin, in the presence of aerobic (as preparation and/or when storage, air leaking is arranged), under the too high temperature and under the existence of solubilized metal as Fe or Ni, be easy to color and generated, and impurities in raw materials promotes the continuous generation of color bodies at the very start.
Verified, overcome the various trials with the unstable related problems of the color of alkanolamine and color, its cost is very high, also is unacceptable from environmental.These trials comprise and utilize fractionation to purify, and by fractional condensation color organizer or their precursor, carbon is handled, and uses sorbing material, various hydrogenation technologies and use reductive agent as sodium borohydride or hydrazine.
US2744938 has described the treatment process of painted responsive organic compound, and this compound is by oxidation or aging the decolouring.This patent has been described specially and has been kept under super-atmospheric pressure in the presence of the hydrogen, and with the method that catalyzer-free solid adsorbent is removed color bodies from alkylphenol, the alkylphenol that will handle is thus separated from solid adsorption material then.
US3207790 has described a kind of method of improving the alkanolamine color, and this method is improved undesirable color by adding the alkali metal borohydride of q.s in the aging step.This hydroborate has tangible dissolving power in alkanolamine, and can remain on after dissolving in the solution, and perhaps alkanolamine under reduced pressure can distill.
US3453183 has described a kind of method of removing aldehyde impurity from thanomin, this method is by forming thanomin and Powdered silicon-dioxide, Powdered silicate, liquid silicon hydrochlorate, perhaps with Powdered alumina mixture, subsequently by vacuum distilling separating alcohol amine.
US3819710 described use catalyzer optionally and optionally catalytic condition improve the color of thanomin and the method for colour stability by hydrogenation, the catalyzer that is used for this method comprises Raney nickel, platinum, palladium or ruthenium.
EP0477593 has described in the presence of water and water-soluble metal hydroborate, and vacuum distilling is with the method for purification and the rough N-dialkyl group-two of decolouring variable color alkanolamine.
Above-mentioned patent confirms to need really to improve the method for alkanolamine and alkylene amines color characteristic.And some method, as using solid adsorbent to improve color, such method can not be applicable to large-scale decolouring fully.And need labour-intensive step to reclaim desired product, with regard to the treatment time, cost of equipment and the processing of paying product want a lot of expenses to put in the treatment process.
Other method as the hydrogenation of coloring impurity, requires expensive Raney nickel, also must periodic replacement.Hydrogenation system also needs specific equipment, and hydrogen supply after mixing and the reduction, filters to remove Raney nickel, and this is owing to distillation in the presence of Raney nickel can be tending towards producing painted and catalyzer being lost activity.
Need a kind of cheap, easy-operating have subtract the alkanolamine that is washed out or the production method of alkylene amines.
According to the present invention, provide a kind of production to have to subtract the alkanolamine that is washed out or the method for alkylene amines, this method comprises under the existence of water at high temperature makes the alkanolamine or the alkylene amines of band look contact for some time with the polymeric solid acid catalyst, is enough to reduce the color of alkanolamine or imido grpup amine.The decolouring step is preferably finished being enough to make water to maintain under the high pressure in the liquid.
The used heterogeneous catalyst of the present invention has advantageously provided multifunctionality, can be with look alkanolamine and alkylene amines with handling continuously in batches.This method is easy to be applicable to general processing units, provides expense low, quality height, the finished product that purity is high.
The inventive method can be effectively has the number of colours of reduction and is about 20PtCo or lower product having platinum-cobalt (PtCo) number up to 100 or the band look alkanolamine and the imido grpup amine of higher color, being processed into.
Relevant with the present invention can be utilized any method well known in the prior art to be prepared,, carry out precision work then, therefrom separate and reclaim needed single component or their mixture as producing crude mixture by decolouring alkanolamine or alkylene amines.By various products refining or that separating technology reclaims generally all is discolored, and its PtCo number is up to 700 or bigger scope, and this is to utilize ASTM method 1209 " Color of Clear liquids(Platinum-Cobalt Scale) " method to measure.
Under without any pretreated situation, purified alkanolamine such as N-aminoethyl ethanolamine (AEEA) can have chromatic number near about 60PtCo or higher.
In addition, utilize pretreated alkanolamine of other known decoloring method or alkylene amines, some of them have lower number of colours at the beginning, variable color during owing to storage temperature rising storage.
The description of following optimum implementation will be referred to the especially decolouring of AEEA of alkanolamine.Yet specified scope comprises alkanolamine and alkylenamines, and as what be surprised to find, when adding water and improving temperature, the present invention is applicable to this compound of two types.
Band look chain hydramine is contacted the coloring impurity that can remove in the alkanolamine with the polymer/solid an acidic catalyst.The polymer/solid an acidic catalyst of preferred class comprises fluoridized ion-exchange polymer (PFIEP), as Nafion
, the registered trademark tetrafluoroethylene of Dupont chemical company and the multipolymer of perfluorinated monomer.Nafion
By tetrafluoroethylene and perfluor-2-(fluorine nyl ethoxy)-the propyl vinyl ether preparation.The preparation of perfluorinated vinyl ether can make tetrafluoroethylene and SO
3Reaction forms the ring-type sultone, and this ring-type sultone is rearranged into fluorine carbonyl methane-sulfonic acid fluoride subsequently.The fluorine propylene oxide reaction of this straight chain analogue and two moles, producing a kind of terminal is the compound of 1-fluorine carbonyl trifluoro ethoxy.This group and Na
2CO
3Together the heating, lose carbonyl fluoride after, obtain perfluorinated vinyl ether.With the alkaligenous form of copolymer resin alkaline hydrolysis of sulfonic acid fluoride form, and then acidifying becomes sulphonic form.
Can buy the polymer/solid an acidic catalyst of sour form, as Nafion
-H or Nafion
-NR50 can buy from Aldrich chemical company.With the form of acid, these materials be by with the perfluorinated polymers main chain on the contiguous sulfonic group of fluorocarbons constitute.The polymer/solid an acidic catalyst can use separately, perhaps adopts method well known in the prior art can be applied to solid support material as silicon oxide as pickling process, aluminum oxide, Bio-Glas, pottery or the like.The surface-area of these carriers and aperture can change, and do not play a decisive role for the operation of polymer/solid an acidic catalyst.
When handling colored alkanolamine or alkylene amines, the amount of catalyst system therefor depends on acid functionality's concentration and intensity, can adopt method well known in the prior art to measure the concentration and the intensity of the acid of polymer/solid an acidic catalyst, as (Hammettindicator) methods such as non-water amine titration.Usually, in the weight of treated material, the amount of used polymer/solid an acidic catalyst is 0.5-10(wt) %.For example, when using Nafion
The time, the amount of catalyst system therefor is the 1-5(wt of treated material amount preferably) %.
Be not bound by any particular theory, can be sure of, under the situation of adding water, the polymer/solid an acidic catalyst is as Nafion
, after the initial weight loss, be stable, and obtain best performance, need not the cyclic regeneration catalyzer.Adding the amount of water, generally is the 1-10(wt that treats that decoloring material is heavy) %, preferred 3-8(wt) %, preferably 4-6(wt) %.
Above-mentioned polymer/solid an acidic catalyst can reduce color bringing into use when anhydrous, yet, the degree that color disappears and takes off, the stability of decolouring product and the stability of catalyst themselves all are low, this technology is not suitable for the process of continuous application.Moreover at high temperature waterless operation can cause catalyst excess loss and catalyzer degradation, and this is because form a large amount of accumulations of paying product in removing the color step.
This technology can be carried out in very wide temperature range, about 150-230 ℃.Reasonable temperature range is 201-215 ℃, preferably from about 205-about 210 ℃.System pressure should be enough high, is liquid phase to guarantee water, is generally 1-100psig, is preferably 20-75psig, is preferably 50-65psig.
In typical embodiment, method of the present invention form or continuous form is in batches carried out, and during with the batch form, discharges the product of handling, and adds new pending product.By using the basket of making by hole sizer easily catalyzer to be remained in the reactor.In the batch formal operations, adopt and stir the efficient that can help to improve catalyzer.The exemplary stir device comprises mechanical stirrer, and rotating speed is 400-1200rpm.
In the operation of continuous form, can use fixed beds, pending product is pumped into by this bed.In this successive technology, mainly be make up water, adopt normal distillation can obtain the product of low color and colour stable.Though also imperfectly understand decolouring mechanism, can believe that adding man-hour continuously, the color organizer destroys in the course of processing, the lightweight fragment that can remove when becoming distillation or the heavy fragment of discharging along with residue.
Should make band look alkanolamine or alkylene amines contact for some time, be enough to produce the decolouring product with the polymer/solid an acidic catalyst.Usually, can be preferably 4-6 hour up to 8 hours for residence time of batch operation or operate continuously, be preferably 4-5 hour.Illustrated as following example, the length of bleaching time depends on the amount that is contained in processing vessel polymer/solid an acidic catalyst, the amount of water in temperature and the system.
Embodiment
Though in the alkylidene group decolouring, used Nafion
(US 4731165) are not added water but this patent has discussion, but are discussed Nafion in technology
Temperature stability, this technology fixed on effective limit of 200 ℃.And then, do not expect and can transfer on the alkanolamine that this is owing to form the processing of color organizer and the difference in the refining process to the decoloration process of alkylene amines.
Below example show that the polymer/solid an acidic catalyst subtracts effect in taking off in the color of alkanolamine.Used solid acid catalyst is the acid Nafion that Dupont chemical company sells
Being used for the initial p tCo number that the thick AEEA of decoloration process has is 79.5.Distillation plant comprises the Oldershaw tower of 5 tower trays, and its dish spacing is 1 inch, and is equipped with the distillation tower head.
Example 1-reference examples
Thick AEEA250 gram is mixed with 10 gram distillation deionized waters.This mixture is packed in the distillation plant, is 0.7psig at pressure, is heated to 205-210 ℃ and reaches 3 hours.Pressure is dropped to 2mmHg, remove distillate part for the first time.In the tower head temperature is 105 ℃, and 2.8mmHg removes second distillate partly, and the 200 untreated AEEA of gram also have the color of 53PtCo.
Example 2-adopts Nafion
Disappear and take off color
300 thick AEEA of gram and 12 gram distillation deionized waters are filled into the Nafion of containing described above
In the water distilling apparatus of pipe (1/8 inch * 1/2 inch cross section of 3 grams).These materials are heated to 205-210 ℃ reach 3 hours.Transfer in the water distilling apparatus with reagent cool to room temperature degree and with supernatant liquor.At 84 ℃, 0.7mmHg removes first distillate partly.Remove second distillate under the same conditions partly, the processed AEEA of 212 grams, the number of colours that has is 9.7PtCo.
Example 3-comparative example
By handling thick AEEA down at 150 ℃ and 180 ℃, initial p tCo number is 79.5.Evaluation temperature the results are shown in following table to the Nafion Effect on Performance, and compares with example 2:
Table 1: temperature is to using Nafion
The influence of decolouring AEEA
Temperature PtCo number
150℃ 38.8
180℃ 21.4
205-210℃ 9.7
(example 2)
Claims (7)
1, a kind of have subtract the alkanolamine that is washed out or the production method of alkylene amines, being included in high temperature adds under the situation of water, the alkanolamine or the alkylene amines of band look are contacted, to reduce the color of said alkanolamine or alkylene amines with the polymer/solid an acidic catalyst.
2, according to the method for claim 1, it is characterized in that: the concentration range of described polymer/solid an acidic catalyst is the 0.5-10(wt of said alkanolamine or alkylene amines weight) %.
3, according to the method for claim 1, it is characterized in that: the water yield of interpolation is alkanolamine or the heavy 1-10(wt of alkylene amines) %.
4, according to the method for claim 1, it is characterized in that: described high temperature is between 150-230 ℃.
5, according to the method for claim 1, it is characterized in that: said have that to subtract the number of colours that the alkanolamine that is washed out or alkylene amines have be that 20PtCo is lower.
6, a kind of have a production method that subtracts the N-aminoethyl ethanolamine that is washed out, and is included in high temperature and adds under the situation of water, band look N-aminoethyl ethanolamine contacted, to reduce the color of said N-aminoethyl ethanolamine with the polymer/solid an acidic catalyst.
According to the method for claim 6, it is characterized in that 7, said have that to subtract the number of colours that the N-aminoethyl ethanolamine that is washed out has be 10PtCo or lower.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/083,987 US5847221A (en) | 1993-06-28 | 1993-06-28 | Method for decolorization of alkanolamines and alkyleneamines |
| US083,987 | 1993-06-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1106792A true CN1106792A (en) | 1995-08-16 |
| CN1060158C CN1060158C (en) | 2001-01-03 |
Family
ID=22181923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94109198A Expired - Fee Related CN1060158C (en) | 1993-06-28 | 1994-06-27 | Method for decolorization of alkanolamines and alkyleneamines |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5847221A (en) |
| EP (2) | EP0764631A1 (en) |
| JP (1) | JPH0717920A (en) |
| KR (1) | KR100215614B1 (en) |
| CN (1) | CN1060158C (en) |
| CA (1) | CA2126794C (en) |
| DE (1) | DE69409040T2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108473416A (en) * | 2015-12-29 | 2018-08-31 | 沙特基础工业全球技术有限公司 | The method to lose lustre in alkanolamine composition and the composition thus produced |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5847221A (en) | 1993-06-28 | 1998-12-08 | Union Carbide Chemicals & Plastics Technology Corporation | Method for decolorization of alkanolamines and alkyleneamines |
| JP3998783B2 (en) * | 1997-11-25 | 2007-10-31 | 花王株式会社 | Process for producing aliphatic amine derivatives |
| DE19942300A1 (en) * | 1999-09-04 | 2001-03-08 | Basf Ag | Process for the preparation of alkanolamines with improved color quality |
| DE10011942A1 (en) * | 2000-03-11 | 2001-09-13 | Basf Ag | Decolorization of alkanolamines, useful in cosmetics industry e.g. in soap, washing agent or shampoo, or as dispersant or emulsifier, uses phosphorous or hypophosphorous acid or compound in heat treatment and distillation |
| US6774264B2 (en) * | 2002-12-06 | 2004-08-10 | Air Products And Chemicals, Inc. | Catalyst to improve the color stability of N,N-dialkylalkanolamines |
| FR2856399A1 (en) * | 2003-06-23 | 2004-12-24 | Bp Lavera Snc | PROCESS FOR THE PREPARATION OF AN ETHANOLAMINE OF IMPROVED COLOR QUALITY |
| JP2005079487A (en) * | 2003-09-03 | 2005-03-24 | Fujitsu Ltd | Magnetoresistance-effect film, and magnetoresistance-effect head and solid-state memory using the same |
| US7425652B2 (en) * | 2005-07-27 | 2008-09-16 | Lyondell Chemical Technology, L.P. | Preparation of alkanolamines |
| FR2947265B1 (en) | 2009-06-25 | 2011-08-05 | Arkema France | PROCESS FOR THE PREPARATION OF ALKYLALCANOLAMINES |
| US8853459B2 (en) * | 2010-09-29 | 2014-10-07 | Dow Global Technologies Llc | Decolorization of amines |
| CN114181099A (en) | 2015-12-11 | 2022-03-15 | 沙特基础工业全球技术有限公司 | Method for reducing color in alkanolamine compositions and compositions produced thereby |
| US20200317603A1 (en) | 2016-11-29 | 2020-10-08 | Basf Se | Process for stabilization of at least monoalkyl-substituted diaminocyclohexanes |
| DE102017125891A1 (en) | 2016-11-29 | 2018-06-28 | Basf Se | Process for the stabilization of at least monoalkyl-substituted diaminocyclohexanes |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744938A (en) * | 1952-07-24 | 1956-05-08 | Universal Oil Prod Co | Removal of color impurities from organic compounds |
| US3207790A (en) * | 1961-07-06 | 1965-09-21 | Dow Chemical Co | Process for reducing the color of discolored alkanolamines |
| US3131132A (en) * | 1962-06-06 | 1964-04-28 | Jefferson Chem Co Inc | Purification of dimethylaminoethanol by acid treatment and distillation |
| US3453183A (en) * | 1964-12-29 | 1969-07-01 | Nippon Catalytic Chem Ind | Method of purifying ethanolamines |
| US3428684A (en) * | 1966-11-02 | 1969-02-18 | Commercial Solvents Corp | Purification of alkanol amines |
| CH519717A (en) | 1970-08-04 | 1972-02-29 | Zellweger Uster Ag | Yarn changing device and use of the same |
| US3723529A (en) * | 1970-10-19 | 1973-03-27 | Jefferson Chem Co Inc | Decolorization of polyethylene polyamines |
| JPS5020047B1 (en) * | 1970-12-28 | 1975-07-11 | ||
| US3723629A (en) | 1971-08-02 | 1973-03-27 | Air Reduction | 1-methoxy-3-h-perfluorobutane as an inhalation anesthetic agent |
| US3819710A (en) * | 1973-01-04 | 1974-06-25 | Olin Corp | Process for improving color and color stability of ethanolamines |
| US4570019A (en) * | 1981-02-25 | 1986-02-11 | Union Carbide Corporation | Method of preparing polyethylene polyamines having improved color |
| US4731165A (en) * | 1985-12-16 | 1988-03-15 | The Dow Chemical Company | Method of decoloration of triethylenetetramine using sulfonic acid ion exchange resins |
| US4737243A (en) * | 1985-12-16 | 1988-04-12 | The Dow Chemical Company | Method for decoloration of triethylenetetramine (TETA) |
| JPS6419902A (en) | 1987-07-15 | 1989-01-24 | Railway Technical Res Inst | Pantograph with windshield body for rapid-transit railway |
| US4956506A (en) * | 1989-12-21 | 1990-09-11 | Conoco Inc. | Vapor-phase hydration of olefins to alcohols in series reactors with intermediate alcohol removal |
| ES2067106T3 (en) * | 1990-09-24 | 1995-03-16 | Atochem North America | PURIFICATION AND DECOLORATION OF INTENSE COLOR ALKYL-ALCANOLAMINES. |
| US5227528A (en) * | 1992-04-30 | 1993-07-13 | The Dow Chemical Company | Decolorization of polyalkylene polyamines |
| US5847221A (en) | 1993-06-28 | 1998-12-08 | Union Carbide Chemicals & Plastics Technology Corporation | Method for decolorization of alkanolamines and alkyleneamines |
-
1993
- 1993-06-28 US US08/083,987 patent/US5847221A/en not_active Expired - Fee Related
-
1994
- 1994-06-27 KR KR1019940015114A patent/KR100215614B1/en not_active IP Right Cessation
- 1994-06-27 CN CN94109198A patent/CN1060158C/en not_active Expired - Fee Related
- 1994-06-27 JP JP6165808A patent/JPH0717920A/en active Pending
- 1994-06-27 CA CA002126794A patent/CA2126794C/en not_active Expired - Fee Related
- 1994-06-28 DE DE69409040T patent/DE69409040T2/en not_active Expired - Fee Related
- 1994-06-28 EP EP96118349A patent/EP0764631A1/en not_active Withdrawn
- 1994-06-28 EP EP94304685A patent/EP0632013B1/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108473416A (en) * | 2015-12-29 | 2018-08-31 | 沙特基础工业全球技术有限公司 | The method to lose lustre in alkanolamine composition and the composition thus produced |
| US11203568B2 (en) | 2015-12-29 | 2021-12-21 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
| US11702382B2 (en) | 2015-12-29 | 2023-07-18 | Sabic Global Technologies B.V. | Methods of reducing color in alkanolamine compositions and compositions produced thereby |
Also Published As
| Publication number | Publication date |
|---|---|
| KR950000645A (en) | 1995-01-03 |
| CA2126794A1 (en) | 1994-12-29 |
| EP0764631A1 (en) | 1997-03-26 |
| DE69409040T2 (en) | 1998-07-30 |
| CA2126794C (en) | 2001-02-13 |
| JPH0717920A (en) | 1995-01-20 |
| EP0632013A2 (en) | 1995-01-04 |
| CN1060158C (en) | 2001-01-03 |
| EP0632013A3 (en) | 1995-11-15 |
| EP0632013B1 (en) | 1998-03-18 |
| DE69409040D1 (en) | 1998-04-23 |
| KR100215614B1 (en) | 1999-08-16 |
| US5847221A (en) | 1998-12-08 |
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